Friday afternoon brings a historic moment between the US and Cuba – the first friendly soccer match between the countries on Cuban soil since 1947 (4 pm ET on ESPN2, UniMás). But serious US Soccer fans know that while it may be the first friendly between the countries in almost 70 years, it’s not the first match overall between them in that entire span.

Indeed, on Sept. 6, 2008, the US visited Cuba for a World Cup Qualifying match at Havana’s Estadio Pedro Marrero, one played while the US embargo still held firm. As bureaucratically complicated as it was for the USMNT to make it there, to fans, the challenge proved almost impossible.

At the time, tourist travel to the island for US citizens was essentially totally illegal; the embargo only allowed visits for humanitarian and other tightly controlled purposes, and spending money there remained verboten. Getting caught could invoke a heavy financial penalty.

Yet a small, hardcore group of USMNT fans decided to risk it all to support the squad. Fans watching the international broadcast quickly spotted them – four men and one woman, enthusiastic as ever in the stands, but their faces obscured with flag bandannas.

Among American soccer diehards, their legend instantly mushroomed, inspiring pages of forum dissection and even fan art.

But their identities remained more or less secret – until now. With President Barack Obama’s easing of travel and trade restrictions with Cuba, both countries enter a new era in relations. And to go with it, four out of the five of the Cuba Cinco agreed to speak with us about what it was like to follow the US there when it wasn’t the case. (One of the five chose to remain anonymous and not comment.)

Here’s an oral history of their audacious trip as told directly by four of the Cuba Cinco – Luis Arguero, Brian Kemp, Jacky Tran, and Douglas Zimmerman. It starts with their early talk online, to the final celebratory moment in the stands, when the whistle blew, and Clint Dempsey’s lone goal gave the US a 1-0 victory to advance.

All photos by Douglas Zimmerman/fandom.futbol, zimpix.com

Photo by Douglas Zimmerman/fandom.futbol

How the Fans Became Five

Like so many other wonders of American soccer fandom, the Cuba Cinco adventure started, essentially, by internet chatter – with a couple of smaller groups of friends coming together on the site BigSoccer.

Jacky Tran: In 2006, I was heavily involved in DJ culture, and I decided to go to Germany for the World Cup, and also to hear music. And one night the World Cup had just ended and I wound up at the club Watergate, and that’s where I met Doug [Zimmerman]. He told me he was there photographing the World Cup, and we became friends.

Douglas Zimmerman: Back when I was in New York, I was talking to Jacky about it, and I mentioned the US had a game coming up in Cuba, and she was like, “Why not go?” and I thought about it, and I said, “Yeah, why not?”

Luis Arguero: I’ve played soccer my whole life – I played D1 in college and followed the team forever; one of my first adventures was going to Venezuela for Copa America. I remember coincidentally staying in the hotel with the team and having dinner with them one time back then because it was like that.

Another time I went to Switzerland for a friendly in Basel and the same thing happened. I’ve been to Azteca a few times, and saw that hostile environment. So this time, I just wanted to witness it firsthand, and tie my love of soccer with my love of exploration.

Brian Kemp: I’m from England and I came over for the World Cup in 1994, met my wife then, got married three weeks later and then more or less stayed here. I became determined to follow the US team.

My wife and I went to a lot of games back then, including the Confederations Cup in Mexico in 1999. Back then you would just stay in the hotel with the players and it was a totally different scene. Then we got to Azteca and there were like 12 fans there, and the players’ wives. US Soccer just gave us tickets because they were surprised people showed up.

So when this came around, it was a tough decision because I had a little one who was only two – but it was a once-in-a-lifetime chance.

Douglas Zimmerman: I went on BigSoccer and asked if anyone was thinking about going and one of my friends responded and said, “Hey, a couple of us are thinking about going,” and that’s all how it kind of started.

Brian Kemp: I thought it was a joke on BigSoccer, so I thought I’d get in on the joke, but then it just spiraled.

Jacky Tran: So months go by and then all of a sudden we have this email chain going, and I remember we were really careful with our language. I think I told people to refer to our destination as “the Florida Keys.”

Photo by Douglas Zimmerman/fandom.futbol

Practical Matters: Getting There

Douglas Zimmerman: I did a lot of research going into it, and it was a little scary, but the risk seemed like maybe anything bad wasn’t really going to happen. And hey, it was a World Cup Qualifying game – a really important game, and we didn’t want to not have any US fans there!

Jacky Tran: Doug and I decided to meet up in Mexico first. We both flew into Cancun and then spent a night in Playa del Carmen first. I did so much research; like if you were American, you couldn’t just go straight to the next gate to Cuba. If you do that, you would get stopped by someone.

So the next day we went back to the airport to the Mexican airline office and bought our ticket in cash. And we were waiting for our flight to Havana and Brian was there.

Douglas Zimmerman: When you would get there, you would get a piece of paper that they would stamp, so you wouldn’t have a stamp in your passport. Then when you would leave Cuba, they just take back the piece of paper.

Brian Kemp: I had actually let my UK passport expire and I was a US citizen, so I had to do it the same way as anyone else. I bought my ticket, too, in cash – I had this big wad of cash, because I didn’t want any record on my credit card. Then I had to change the Mexican pesos into Cuban pesos when we got there.

Luis Arguero: I bought my ticket in Mexico, too, and with the passport stamp – I mean I speak Spanish fluently, so I just told the guy, “Don’t stamp my passport,” and he didn’t. I think my friend might have slipped him a $20 bill or something.

Jacky Tran: I remember at the airport, all of us had to go to the bathroom so many times, we were so excited.

The Night Before

Some of the Cinco stayed in a hotel, while others chose for private homestays – but all five convened the night before the game to hang out and go over their own plan.

Jacky Tran: The night before, we all met up for drinks and Brian wanted to meet up with the journalist Grant Wahl, from Sports Illustrated. We were all like, yeah, whatever. So we meet up in this plaza and he was with his photographer, and we have a bunch of booze, and he asked if he could get some quotes from us, and we’re like, “Yeah, but you can’t reveal our identities.”

Grant Wahl: I had put out a query in one of my mailbag columns because I knew I was a journalist accredited to cover it, but I didn’t think any fans would be able to go, which I thought was kind of a bummer. But I got a response to that query.

We got in touch and they were up for getting together, and we got together at this really cool outdoor bar. We talked in detail about their anonymity, because the penalty for getting caught was actually pretty severe. But we agreed to mask their identity very carefully because it was going to be published even before they got back.

Jacky Tran: I’m pretty political, and in this situation I ended up being the intense, fiery one. I was like, “This is unconstitutional, the US government is going to dictate to Americans where they’re allowed to spend their money? The whole policy is ridiculous, and I would like to stand up for any citizen’s right to travel to Cuba!”

And the other guys are like, “Oh s*,” because this was not meant to be a political trip for this statement. It wasn’t for me either. We all just wanted to go down there and enjoy the game, and have a good time. But thinking about the whole process started firing me up.

Photo by Douglas Zimmerman/fandom.futbol

Game Day

The environment the Cuba Cinco found was hardly hostile.

Luis Arguero: We all met up in the lobby of the Hotel Nacional and we grabbed an old 1950s Chevy taxi into the stadium. Obviously we didn’t have tickets ahead of time, so we just walked up to the box office and got tickets, just like that – mind you, at an inflated rate for visitors, which was definitely less than $10. The local rate was like $1.25 or something.

Brian Kemp: I’m almost sure we got a pink Cadillac to the game. And then we got to where you would buy tickets, because we didn’t know it would sell out, and it was this tiny kiosk that looked like it might sell ice cream or something.

Jacky Tran: It was really surreal. I just remember like getting out of the car – maybe we took two cars, I don't know. Anyway, we got out of our vehicle, and next thing I knew it was just cameras and people running around. You know, it was such a blur.

Luis Arguero: The outfits we wore, that was a culmination of all of us getting together and saying, hey, we should probably not show who we are.

Douglas Zimmerman: It was national television – so just in case, we decided it wasn’t worth it to show ourselves. We ended up buying these Cuban, Communist-style hats and bandannas that covered our faces, but some of us had these American flag bandannas already. So if you see photos, it wound up being this mix.

Luis Arguero: The bandannas we decided on early on. Looking back, I guess the outfit maybe attracted even more attention and made us stand out even more – which is funny, because now people wear bandannas to games all the time.

Jacky Tran: The Cubans, they knew that as an American you had to go through so much to get down there, that they were really appreciative of anyone who came.

The fans were cheering for Cuba, but I don't think any of the Cubans expected Cuba to win per se. They were just kind of there for the vibe, and they seemed to be really excited we had come down.

Luis Arguero: People wanted pictures with us left and right, and I was doing all these Spanish-language interviews.

Douglas Zimmerman: It was really interesting because most of the coverage was people just curious about why we were there, since we were breaking the law, basically, to be there.

Actually, there was one other American guy who was supposedly there for the game, and we kind of had our doubts that this guy was a soccer fan. He was like, “Oh yeah, I work in Russia,” and had this weird story that didn’t make sense, and he didn’t really know soccer and had, like, a green shirt.

He might have just been an American, but we did kind of have our doubts about him. So it wasn’t the Cuban journalists we were worried about – it was that guy. One of us was like, “Yeah dude, he’s definitely a spy. He’s definitely spying on us.”

The game remained scoreless and scrappy – until Clint Dempsey scored the lone goal in the 40th minute.

Luis Arguero: People gave us high-fives and congratulated us. It wasn’t like the Azteca.

Douglas Zimmerman: There was one Cuban guy with an American shirt and flag who was like, “I love America!” and kept coming over.

The small contingent of USMNT fans who traveled to cheer on the USA in a 2010 CONCACAF World Cup in Havana on September 6, 2008. Photo courtesy Enrique De La Osa / Reuters

Grant Wahl: I remember the guy in full stars and stripes regalia, and I have a follow-up article about him in which he said the game was “the five happiest hours of [his] life.” He was amazing – and I remember also with him being really careful and making sure he wanted me to report his name.

Brian Kemp: The game was pretty one-sided. But one memory I do have is when the lights in the stadium went out, but everyone kept on playing. It was part and parcel of the whole thing, really. It felt like the equivalent of a high-school stadium.

Douglas Zimmerman: The end of the game was pretty cool because Don Garber and Sunil Gulati and some other people actually came over and shook our hands, thanking us for coming out.

Jacky Tran: Later after the game, we were drunkenly singing “Guantanamera” all night along the Malecon, the sea wall that runs along the city. And everywhere Cubans loved it, and they would just come back and join us and sing it. I remember there were people that were just world-class singers that would kind of come in and start having a solo, and it was really incredible.

Photo by Douglas Zimmerman/fandom.futbol

Photo by Douglas Zimmerman/fandom.futbol

Back to Real Life – and to a Fandom Legacy

Jacky Tran: I remember we all met up back at the Hotel Nacional, and I think Doug got his laptop and got on the internet and he was like, “Oh my gosh, we’re all over the message boards.” Grant [Wahl] had written this huge article about us that was on the home page of Sports Illustrated, and forums were blowing up.

Luis Arguero: When we got back on the internet we could see that from Sports Illustrated it had gotten to ESPN and all these sites, and on the broadcast they were focusing on us, during the national anthem and stuff. And I guess we kind of got this following.

Brian Kemp: We did have a moment where we were standing in this hotel lobby over this crappy internet connection, and we looked at each other and thought, “Oh, holy s*.”

Jacky Tran: We were still going to stay in Cuba for like a week after the game, but a huge hurricane blew through the island. So we had to leave.

Douglas Zimmerman: At the time, I was a little worried people would figure out who I was, but once I got back I wasn’t worried. I learned that the Cuban people were great and wanted to have an exchange. It’s good to travel and see things are not like what everyone tells you.

I think it’s great that American fans get to go now. I hope they have a great time and really enjoy it. Having said that, though, it was kind of fun when it was hard and we were the only ones who did it.

Brian Kemp: There was this moment where we had the pink Cadillac, and we were driving along the Malecon to the edge of town, singing USA songs, and I remember thinking, “Wow, the risk and everything – this moment made it all worth it.”

Jacky Tran: We all still keep in touch. You know, every once in a while something pops up about Cuba, or about the soccer team, and we’ll send it to each other.

Luis Arguero: Looking back on it all, I feel proud. It wasn’t something we were doing cause we wanted to create a name for ourselves or be rebellious against our government. We are just soccer fans who wanted to support our soccer team, in a place where the government wasn’t really allowing us to go. But we weren’t gonna let that restriction stop us — I’m a fan of the US national team, and I’ll do whatever I can to be there and support them.

Photo by Douglas Zimmerman/fandom.futbol